Stadium: Court 7 Round: 164 Ground: Clay
| Challenger Guadalajara | 2018/04/20 21:00 | Pedja Krstin v Darian King | 6-2,1-6,6-2 |
| ATP Houston | 2019/04/06 19:55 | Peter Polansky v Darian King | 4-6,1-6 |
| Challenger Monterrey | 2019/04/04 18:35 | Tennys Sandgren v Darian King | 7-6,4-6,6-2 |
| Challenger Monterrey | 2019/04/02 19:45 | Evan King v Darian King | 6-4,6-7,1-6 |
| ATP Miami | 2019/03/18 14:00 | Darian King v Denis Istomin | 4-6,6-3,6-7 |
| ATP Indian Wells | 2019/03/06 02:10 | Darian King v Elias Ymer | 6-1,1-6,2-6 |
| Challenger Indian Wells | 2019/02/26 00:20 | Darian King v Kamil Majchrzak | 4-6,3-6 |
| ATP Delray Beach | 2019/02/18 23:00 | Lloyd Harris v Darian King | 7-6,6-3 |
| ATP Delray Beach | 2019/02/17 17:45 | Alexei Popyrin v Darian King | 6-7,3-6 |
| ATP Houston | 2019/04/06 20:40 | Pedja Krstin v Marcos Giron | 6-4,6-1 |
| Challenger Monterrey | 2019/04/03 17:00 | Pedja Krstin v Alexander Bublik | 6-1,3-6,4-6 |
| Challenger Monterrey | 2019/04/02 20:20 | Pedja Krstin v Lucas Gomez | 6-0,6-3 |
| Challenger Phoenix | 2019/03/13 17:00 | Pedja Krstin v Peter Gojowczyk | 4-6,4-6 |
| Challenger Phoenix | 2019/03/11 18:50 | Ramkumar Ramanathan v Pedja Krstin | 2-6,4-6 |
| Challenger Indian Wells | 2019/02/26 18:00 | Alex Bolt v Pedja Krstin | 6-3,6-4 |
| Challenger Indian Wells | 2019/02/25 21:55 | Pedja Krstin v Ruben Bemelmans | 6-3,6-4 |
| Challenger Morelos | 2019/02/19 19:00 | Pedja Krstin v Tomas Barrios Vera | 5-7,4-6 |